Abstract
A novel water-compatible molecularly imprinted resin was prepared in a green solvent deep eutectic solvent (DES). Resorcinol and melamine, as functional monomers with an abundant hydrophilic group, such as –OH, –NH2 and –NH–, were introduced into the molecularly imprinted resin (MIR). Three DESs (choline chloride-ethylene glycol, tetramethylammonium bromide-ethylene glycol and tetramethylammonium chloride-ethylene glycol) were used to synthesize the molecularly imprinted resin and the resulting deep eutectic solvent-based molecularly imprinted resins were characterized by particle size analysis, elemental analysis, scanning electron microscopy, Fourier transform infrared spectroscopy and thermogravimetric analysis. The resulting deep eutectic solvent-based molecularly imprinted resins were then applied to the adsorption of quinolones (ofloxacin) in water. The adsorption process of deep eutectic solvent-based molecularly imprinted resin followed the static adsorption model, Langmuir isotherm (R2 ≥ 0.9618) and kinetic model pseudo-second-order (R2 > 0.9814). The highest theory adsorption ability of the three kinds of deep eutectic solvent-based molecularly imprinted resins was more than 23.79 mg/g. The choline chloride-ethylene glycol-based MIR was applied to solid-phase extraction for the determination and purification of quinolones (e.g., ciprofloxacin and ofloxacin). The detection limit of deep eutectic solvent-based molecularly imprinted resin-solid-phase extraction method was less than 0.018 mg/L. The recoveries of the deep eutectic solvent-based molecularly imprinted resin-solid-phase extraction method at three spiked levels were 88.7–94.5%, with a relative standard deviation of ≤4.8%. The novel deep eutectic solvent-based molecularly imprinted resin-solid-phase extraction method is a simple, selective and accurate pre-treatment method and can be used to determine the quinolones in environmental water.
Highlights
Molecularly imprinted polymers (MIPs) have been adopted as a kind of tailor-made receptor with specific molecular recognition sites in terms of the size, shape and functional groups.The main principles of the molecularly imprinted technique (MIT) are based on incorporating functional monomers with a template molecule to form a pre-complex via covalent or non-covalent bonds [1,2,3,4]
Fourier transform infrared (FTIR) spectroscopy revealed a peak for the hydroxyl stretching vibration at 3330 cm−1, which was attributed to the existence of EG
This confirmed that DES1, DES2 and DES3 had been entrapped into the molecularly imprinted resin (MIR)
Summary
Molecularly imprinted polymers (MIPs) have been adopted as a kind of tailor-made receptor with specific molecular recognition sites in terms of the size, shape and functional groups. The excellent thermal stability, non-flammability and solubility of DESs can be applied to chemical synthesis, extraction and separation [24,25] In this protocol, the hydrophilic DES was selected as the solvent medium to prepare the DES-based MIR (DES-MIR). DESs, as solvent media, provided an extra ionic interaction that is theoretically stronger than a hydrogen-bond This characteristic makes it more resistant to the interference of conventional solvent molecules during the process of imprinting and recognition toward analytes. A new water-compatible MIR was synthesized in DES solvent media with hydrophilic resorcinol and melamine monomers and formaldehyde cross-linker, which introduced abundant hydrophilic groups into the resin structure.
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